Examples of a prior document related to the present invention include the following documents.
Patent Document 1: DE 1021858 A
Patent Document 2: U.S. Pat. No. 5,750,590
Patent Document 3: JP-A-11-106380
Patent Document 4: EP 1,069,120 A
Patent Document 5: JP-A-2002-80581
Patent Document 6: JP-A-2000-302774
Patent Document 7: JP-A-2003-55359
Non Patent Document 1: H. Sasaki and J. V. Crivello, J. Macromol. Sci., Part A-Pure Appl. Chem. (Marcel Dekker, Inc.), 1992, A29(10), P. 915-930
Non Patent Document 2: J. V. Crivello and H. Sasaki, J. Macromol. Sci., Part A-Pure Appl. Chem. (Marcel Dekker, Inc.), 1993, A30(2&3), P. 189-206
A compound having an oxetane ring (hereinafter referred to as the “oxetane compound”) is a compound that has been attracting attention in recent years because it functions as a monomer which can be subjected to photoinitiating cationic polymerization or which can be cured. In particular, a polyfunctional oxetane compound having two or more oxetane rings in one molecule is known to show high reactivity (see, for example, DE 1021858 A).
DE 1021858 A describes, as an example of a polyfunctional oxetane compound that has been conventionally reported, an aromatic compound having two or more oxetane rings (hereinafter referred to as the “aromatic oxetane compound”) and represented by a general formula (7):
where A1 represents an aromatic residue which is divalent or more, R1's each represent a hydrogen atom or an organic residue, and n1 represents an integer larger than 1.
In addition, various polyfunctional aliphatic and aromatic oxetane compounds have been disclosed in, for example, J. Macromol. Sci., Part A-Pure Appl. Chem. 1992, A29 (10), P. 915-930 and J. Macromol. Sci., Part A-Pure Appl. Chem. 1993, A30 (2 & 3), P. 189-206, U.S. Pat. No. 5,750,590, JP-A-11-106380, EP 1,069,120 A, and JP-A-2002-80581.
In addition, JP-A-2000-302774 discloses alicyclic oxetane compounds serving as a 1,4-cyclohexanedimethanol derivative and a 4,8-bis(hydroxymethyl)tricyclo[5,2,1,02,6]decane derivative, and a process for producing each of them. However, the production process has a problem in that a production step is so complicated that a production cost is high because the process involves: converting 3-alkyl-3-hydroxymethyloxetane into a sulfonate once; reacting the resultant sulfonate and a diol with each other in the presence of a base; and isolating the resultant through vacuum distillation.
Furthermore, JP-A-2003-55359 discloses a process for producing a bis(hydroxymethyl)tricyclo[5,2,1,02,6]decane derivative having an oxetane ring. However, the production process, which involves reacting 3-alkyl-3-chloromethyloxetane and a bis(hydroxymethyl)alicyclic compound with each other in the presence of an alkali, is not sufficiently satisfactory because the yield of a target product is low owing to a low reaction rate and a side reaction.